What I did for the gig: Robert Shapiro

“What I did for the gig” is a weekly web feature that chronicles the outlandish, risky and comical strategies that residential and commercial real estate brokers have used to land listings, clients and jobs.

Negotiating for space in Midtown Manhattan is a tough business, especially when faced with an uninterested seller and a looming deadline. For Robert Shapiro, a broker who orchestrated a 1986 REBNY award-winning assemblage deal for the Crowne Plaza Times Square, the challenge called for a stunt that would let him rise to the occasion. Literally.

In preparation of the hotel development spearheaded by William Lie Zeckendorf, Shapiro had just completed a buy-out of a myriad of seedy adult establishments on the west side of Broadway between West 48th and West 49th streets from multiple owners, including John Zaffarano, whose father Mickey allegedly ran the pornography business for the Mafia syndicate, and Genovese crime boss Matthew “Matty the Horse” Ianniello. But for the project to be viable, it was necessary to acquire a lot at 209 West 49th Street, which was owned by Ralph Friedman, the owner of film company Magno Sound.

In March 1985, Shapiro first approached Friedman, who was 80 percent through the renovation of the building that he intended to make the new home of Magno Sound. Friedman repeatedly rebuffed his calls and visits, Shapiro recalls, and eventually asked his secretary to tell Shapiro to stop contacting him. “He was focused in on doing his thing and didn’t want to do what we did,” he said, and added that time was of the essence due to a sunset provision on the zoning permissions.

That’s when Shapiro, with the help of his advertising copywriter sister, came up with his pièce de resistance.

“In order to change his attitude, I called up a balloon service and ordered the biggest bunch of helium balloons that they had,” Shapiro recalled.

Emblazoned across the balloons were the words “Air Rights,” to stress to Friedman that the buyers would, as a last resort, buy air rights for the property and use them to eventually negotiate a full sale. Shapiro followed this up with a visit to Friedman’s office, where he was greeted with great mirth by his staff.

“It was at this time,” Shapiro said, “that Mr. Friedman came out, laughed at me, said ‘You are too much!’ and promised he would work something out.” Friedman eventually signed a $10 million deal for the property in May 1986. “It just changed the mood,” Shapiro said.

It was a slow courtship, however, and even required Shapiro to discard his “investment banking grays” in response to jibes from Friedman’s staff. “To get into the swing of things,” Shapiro said, “I would show up in a satin Miami Vice jacket with a flamingo pink lining that I had appropriated from my nephew.”

Today, the 843,131-square-foot, 795-room hotel at 1601 Broadway is the flagship hotel of the Crowne Plaza brand, and includes two business centers, the Broadway 49 Bar & Lounge, and one of the city’s largest hotel-based fitness facilities, the New York Sports Club.

But Shapiro was quick to caution against relying on such stunts, stressing that they should only be used as a last resort. “Usually we’re very serious in what we do and not doing flaky things like this,” he said. “When we’re dealing with professional people, we keep it professional. But in this case, it worked!”

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I’ve worked with Bob on and off for nesrly 40 years and he is one of the smartest, most knowledgeable and hard working brokers in the city. He seems to know every property and own on the island of Manhattan.